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Automated sending is only useful if your messages keep landing in inboxes and always sound like you. HelloSky enforces sending guardrails on every mailbox and routes AI-personalized email through an approval step.

Delivery guardrails

Sequence sends respect these limits per connected mailbox:
  • Send window. Sequence emails go out between 8:00 am and 6:00 pm in your local time by default.
  • Weekdays only. Weekend sending is off by default and can be enabled per mailbox.
  • Daily cap. At most 120 emails per rolling 24 hours per mailbox, counting both sequence and one-off sends.
  • Natural timing. Each send is scheduled with a randomized offset of up to 45 minutes, so your follow-ups don’t fire at machine-precise intervals.
Anything that can’t be sent right now (outside the window, over the cap) simply waits its turn; nothing is dropped. Adjust the window under Settings → Email accounts → Delivery schedule: timezone, window start and end, and whether weekends are allowed. Tighten it if your candidates are in a different timezone or you want sends confined to business hours.

Approvals for AI-personalized email

Any sequence step can be marked Personalize each email with AI: instead of sending the template as written, HelloSky drafts a unique email for each recipient from their profile. Personalized drafts never send silently; each one waits in the approval queue until a person has reviewed it.
The Approvals tab with AI-personalized drafts waiting for review
In Outreach → Approvals, review each pending draft and either Approve & send it, Edit it first, Regenerate it if the draft misses the mark, or Skip person to drop that step for that recipient. Toggle between Mine and Everyone to review your own queue or the whole team’s.

The Outreach dashboard

The Outreach page pulls the whole operation together for your organization:
The Outreach Overview with send and reply totals, a sends-per-day chart, and per-sequence performance
  • Overview: emails sent and replies over the last 30 days, active enrollments, a sends-per-day chart covering the past 30 days plus the next 7 days of scheduled sends, and a per-sequence table with owner, enrollment counts, and reply rate.
  • Replies: every response in one place. Click a reply to read the full thread, fetched live from your mailbox.
  • Approvals: the pending AI draft queue described above.
  • Activity: a log of everything sent, with per-email status.
The Replies tab with a full email thread open, showing the reply that stopped the sequence
Reply rate is the number that matters. If it’s low, shorten your opener and make the first sentence about them, not about you.